NPASS Compound

Structure

NPC474404 OpenBabel07101719152D 23 27 0 0 1 0 0 0 0 0999 V2000 -3.2103 0.8106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3779 -2.1184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2932 1.6698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4723 -0.1706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1953 1.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6930 0.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6179 -1.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8434 0.1801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4831 -0.8906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9889 -0.9279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 1.3309 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2360 -0.9093 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5963 0.1614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3780 -2.1334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2252 -0.1893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8650 -1.2599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9781 -0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8909 -2.9918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3781 -2.1483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 10 1 0 0 0 0 7 13 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 6 0 0 0 13 17 1 6 0 0 0 13 18 1 0 0 0 0 14 17 1 6 0 0 0 14 20 1 0 0 0 0 15 19 1 1 0 0 0 15 20 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 1 1 6 0 0 0 18 2 1 1 0 0 0 19 3 1 1 0 0 0 19 23 1 0 0 0 0 20 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	335.428
LogP:	4.122
LogD:	3.235
LogS:	-4.125
# Rotatable Bonds:	1
TPSA:	49.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	5.873
Fsp3:	0.95
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.121
MDCK Permeability:	2.5054747311514802e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.369
Plasma Protein Binding (PPB):	88.56810760498047%
Volume Distribution (VD):	0.423
Pgp-substrate:	10.02701473236084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.609
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.732
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	2.072
Half-life (T1/2):	0.326

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.679
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.303
Skin Sensitization:	0.925
Carcinogencity:	0.47
Eye Corrosion:	0.929
Eye Irritation:	0.817
Respiratory Toxicity:	0.962

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC474404

Natural Product ID:	NPC474404
*Common Name:**	REINKLWVLCQOIC-IELLNMBKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	REINKLWVLCQOIC-IELLNMBKSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-17-8-4-9-18(2,16(21)22)13(17)7-10-20-11-12(5-6-14(17)20)19(3)15(20)23-19/h12-15H,4-11H2,1-3H3,(H,21,22)/t12-,13-,14-,15-,17+,18+,19-,20+/m0/s1
SMILES:	OC(=O)[C@]1(C)CCC[C@@]2([C@@H]1CC[C@]13[C@H]2CC[C@@H](C1)[C@]1([C@@H]3O1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466783
PubChem CID:	16058231
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713399]
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104491]
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	31.25	ug.mL-1	PMID[469701]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC474404 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	3430
0.2-0.3	15301
0.3-0.4	8453
0.4-0.5	5729
0.5-0.6	6165
0.6-0.7	2645
0.7-0.8	497
0.8-0.85	107
0.85-0.9	24
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC259173
0.8831	High Similarity	NPC472853
0.8816	High Similarity	NPC199965
0.8816	High Similarity	NPC476732
0.8767	High Similarity	NPC469940
0.8684	High Similarity	NPC477919
0.8684	High Similarity	NPC180199
0.863	High Similarity	NPC477850
0.863	High Similarity	NPC477929
0.8608	High Similarity	NPC477935
0.8608	High Similarity	NPC477936
0.8533	High Similarity	NPC280026
0.8533	High Similarity	NPC167702
0.85	High Similarity	NPC472847
0.8493	Intermediate Similarity	NPC64466
0.8493	Intermediate Similarity	NPC252032
0.8493	Intermediate Similarity	NPC196197
0.8493	Intermediate Similarity	NPC321732
0.8493	Intermediate Similarity	NPC476734
0.8493	Intermediate Similarity	NPC324607
0.8493	Intermediate Similarity	NPC319671
0.8493	Intermediate Similarity	NPC469941
0.8481	Intermediate Similarity	NPC58631
0.8481	Intermediate Similarity	NPC77311
0.8472	Intermediate Similarity	NPC474221
0.8472	Intermediate Similarity	NPC478180
0.8472	Intermediate Similarity	NPC130459
0.8442	Intermediate Similarity	NPC477918
0.8421	Intermediate Similarity	NPC212733
0.8421	Intermediate Similarity	NPC477934
0.84	Intermediate Similarity	NPC310766
0.84	Intermediate Similarity	NPC474123
0.8354	Intermediate Similarity	NPC261616
0.8333	Intermediate Similarity	NPC477931
0.8333	Intermediate Similarity	NPC268736
0.8333	Intermediate Similarity	NPC42060
0.8312	Intermediate Similarity	NPC477933
0.8312	Intermediate Similarity	NPC477932
0.8312	Intermediate Similarity	NPC4209
0.8289	Intermediate Similarity	NPC472854
0.825	Intermediate Similarity	NPC12933
0.8243	Intermediate Similarity	NPC474962
0.8228	Intermediate Similarity	NPC80891
0.8228	Intermediate Similarity	NPC472310
0.8228	Intermediate Similarity	NPC201276
0.8205	Intermediate Similarity	NPC207010
0.8205	Intermediate Similarity	NPC298168
0.8205	Intermediate Similarity	NPC317913
0.8205	Intermediate Similarity	NPC143133
0.8182	Intermediate Similarity	NPC27349
0.8182	Intermediate Similarity	NPC472311
0.8182	Intermediate Similarity	NPC24014
0.8171	Intermediate Similarity	NPC319909
0.8148	Intermediate Similarity	NPC289486
0.8148	Intermediate Similarity	NPC61107
0.8133	Intermediate Similarity	NPC108131
0.8125	Intermediate Similarity	NPC477851
0.8101	Intermediate Similarity	NPC329117
0.8101	Intermediate Similarity	NPC185465
0.8101	Intermediate Similarity	NPC171426
0.8101	Intermediate Similarity	NPC34046
0.8101	Intermediate Similarity	NPC471045
0.8101	Intermediate Similarity	NPC324700
0.8101	Intermediate Similarity	NPC224802
0.8101	Intermediate Similarity	NPC80089
0.8068	Intermediate Similarity	NPC470031
0.8052	Intermediate Similarity	NPC477930
0.8049	Intermediate Similarity	NPC245866
0.8046	Intermediate Similarity	NPC472231
0.8046	Intermediate Similarity	NPC472232
0.8026	Intermediate Similarity	NPC473267
0.8026	Intermediate Similarity	NPC320549
0.8026	Intermediate Similarity	NPC478227
0.8026	Intermediate Similarity	NPC151018
0.8026	Intermediate Similarity	NPC197701
0.8026	Intermediate Similarity	NPC156277
0.8026	Intermediate Similarity	NPC58057
0.8023	Intermediate Similarity	NPC77756
0.8	Intermediate Similarity	NPC131892
0.8	Intermediate Similarity	NPC327728
0.8	Intermediate Similarity	NPC6120
0.8	Intermediate Similarity	NPC476176
0.8	Intermediate Similarity	NPC31302
0.8	Intermediate Similarity	NPC213178
0.8	Intermediate Similarity	NPC320144
0.8	Intermediate Similarity	NPC245029
0.7976	Intermediate Similarity	NPC92139
0.7976	Intermediate Similarity	NPC474448
0.7976	Intermediate Similarity	NPC472272
0.7976	Intermediate Similarity	NPC472505
0.7975	Intermediate Similarity	NPC264602
0.7975	Intermediate Similarity	NPC475031
0.7975	Intermediate Similarity	NPC171658
0.7955	Intermediate Similarity	NPC470423
0.7952	Intermediate Similarity	NPC473336
0.7952	Intermediate Similarity	NPC263974
0.7952	Intermediate Similarity	NPC471044
0.7949	Intermediate Similarity	NPC179858
0.7949	Intermediate Similarity	NPC72444
0.7949	Intermediate Similarity	NPC273366
0.7931	Intermediate Similarity	NPC52756
0.7927	Intermediate Similarity	NPC242771
0.7927	Intermediate Similarity	NPC311642
0.7927	Intermediate Similarity	NPC170985
0.7927	Intermediate Similarity	NPC102156
0.7927	Intermediate Similarity	NPC148740
0.7927	Intermediate Similarity	NPC164289
0.7927	Intermediate Similarity	NPC100366
0.7922	Intermediate Similarity	NPC232112
0.7882	Intermediate Similarity	NPC134197
0.7867	Intermediate Similarity	NPC473225
0.7848	Intermediate Similarity	NPC471046
0.7831	Intermediate Similarity	NPC472744
0.7831	Intermediate Similarity	NPC471037
0.7821	Intermediate Similarity	NPC272359
0.7821	Intermediate Similarity	NPC254340
0.7805	Intermediate Similarity	NPC469745
0.7805	Intermediate Similarity	NPC280781
0.7805	Intermediate Similarity	NPC48756
0.7792	Intermediate Similarity	NPC89310
0.7792	Intermediate Similarity	NPC472309
0.7765	Intermediate Similarity	NPC80590
0.7763	Intermediate Similarity	NPC178541
0.7753	Intermediate Similarity	NPC206878
0.775	Intermediate Similarity	NPC23884
0.775	Intermediate Similarity	NPC212453
0.775	Intermediate Similarity	NPC66105
0.7738	Intermediate Similarity	NPC474996
0.7733	Intermediate Similarity	NPC41542
0.7722	Intermediate Similarity	NPC21220
0.7722	Intermediate Similarity	NPC174964
0.7722	Intermediate Similarity	NPC195155
0.7722	Intermediate Similarity	NPC97534
0.7722	Intermediate Similarity	NPC186851
0.7722	Intermediate Similarity	NPC125767
0.7711	Intermediate Similarity	NPC13494
0.7711	Intermediate Similarity	NPC328007
0.7711	Intermediate Similarity	NPC317066
0.7711	Intermediate Similarity	NPC30583
0.7711	Intermediate Similarity	NPC121121
0.7701	Intermediate Similarity	NPC472234
0.7701	Intermediate Similarity	NPC472233
0.7683	Intermediate Similarity	NPC470609
0.7667	Intermediate Similarity	NPC215570
0.7662	Intermediate Similarity	NPC476731
0.7654	Intermediate Similarity	NPC243594
0.7654	Intermediate Similarity	NPC31031
0.764	Intermediate Similarity	NPC476189
0.764	Intermediate Similarity	NPC228700
0.7625	Intermediate Similarity	NPC472486
0.7625	Intermediate Similarity	NPC5767
0.7625	Intermediate Similarity	NPC470145
0.7625	Intermediate Similarity	NPC472487
0.7625	Intermediate Similarity	NPC475742
0.7619	Intermediate Similarity	NPC15821
0.7619	Intermediate Similarity	NPC292458
0.7619	Intermediate Similarity	NPC217559
0.7619	Intermediate Similarity	NPC170862
0.7619	Intermediate Similarity	NPC327451
0.7619	Intermediate Similarity	NPC268578
0.7595	Intermediate Similarity	NPC133922
0.7595	Intermediate Similarity	NPC472945
0.7595	Intermediate Similarity	NPC472944
0.759	Intermediate Similarity	NPC472229
0.759	Intermediate Similarity	NPC472230
0.7586	Intermediate Similarity	NPC33398
0.7586	Intermediate Similarity	NPC183374
0.7586	Intermediate Similarity	NPC255176
0.7586	Intermediate Similarity	NPC211162
0.7586	Intermediate Similarity	NPC4309
0.7582	Intermediate Similarity	NPC116683
0.7564	Intermediate Similarity	NPC195530
0.7561	Intermediate Similarity	NPC220379
0.7558	Intermediate Similarity	NPC12774
0.7558	Intermediate Similarity	NPC472745
0.7558	Intermediate Similarity	NPC70661
0.7558	Intermediate Similarity	NPC302111
0.7556	Intermediate Similarity	NPC477495
0.7534	Intermediate Similarity	NPC306750
0.7532	Intermediate Similarity	NPC295788
0.7531	Intermediate Similarity	NPC221420
0.7531	Intermediate Similarity	NPC307865
0.7531	Intermediate Similarity	NPC471151
0.7531	Intermediate Similarity	NPC476233
0.7528	Intermediate Similarity	NPC150383
0.75	Intermediate Similarity	NPC24556
0.75	Intermediate Similarity	NPC215029
0.75	Intermediate Similarity	NPC24705
0.75	Intermediate Similarity	NPC56962
0.75	Intermediate Similarity	NPC159789
0.75	Intermediate Similarity	NPC116146
0.75	Intermediate Similarity	NPC24772
0.75	Intermediate Similarity	NPC476733
0.7473	Intermediate Similarity	NPC205173
0.7471	Intermediate Similarity	NPC202937
0.7471	Intermediate Similarity	NPC252714
0.7471	Intermediate Similarity	NPC33768
0.747	Intermediate Similarity	NPC206735
0.747	Intermediate Similarity	NPC474714
0.7468	Intermediate Similarity	NPC109510

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC474404 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	3464
0.2-0.3	3701
0.3-0.4	920
0.4-0.5	287
0.5-0.6	239
0.6-0.7	127
0.7-0.8	23
0.8-0.85	13
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9178	High Similarity	NPD3702	Approved
0.8767	High Similarity	NPD5777	Approved
0.8533	High Similarity	NPD6113	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD3698	Phase 2
0.8378	Intermediate Similarity	NPD4245	Approved
0.8378	Intermediate Similarity	NPD4244	Approved
0.8333	Intermediate Similarity	NPD4224	Phase 2
0.8312	Intermediate Similarity	NPD6117	Approved
0.8205	Intermediate Similarity	NPD6116	Phase 1
0.8101	Intermediate Similarity	NPD6114	Approved
0.8101	Intermediate Similarity	NPD6115	Approved
0.8101	Intermediate Similarity	NPD6697	Approved
0.8101	Intermediate Similarity	NPD6118	Approved
0.8026	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6081	Approved
0.8	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4789	Approved
0.7867	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD5360	Phase 3
0.7564	Intermediate Similarity	NPD4758	Discontinued
0.75	Intermediate Similarity	NPD3703	Phase 2
0.7442	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4788	Approved
0.7333	Intermediate Similarity	NPD8034	Phase 2
0.7333	Intermediate Similarity	NPD8035	Phase 2
0.726	Intermediate Similarity	NPD3198	Approved
0.7229	Intermediate Similarity	NPD3671	Phase 1
0.7215	Intermediate Similarity	NPD4787	Phase 1
0.7191	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7146	Approved
0.7159	Intermediate Similarity	NPD7521	Approved
0.7159	Intermediate Similarity	NPD7334	Approved
0.7159	Intermediate Similarity	NPD6684	Approved
0.7159	Intermediate Similarity	NPD6409	Approved
0.7159	Intermediate Similarity	NPD5330	Approved
0.7128	Intermediate Similarity	NPD6084	Phase 2
0.7128	Intermediate Similarity	NPD6083	Phase 2
0.7097	Intermediate Similarity	NPD5695	Phase 3
0.7065	Intermediate Similarity	NPD6399	Phase 3
0.7053	Intermediate Similarity	NPD5696	Approved
0.7024	Intermediate Similarity	NPD5364	Discontinued
0.7	Intermediate Similarity	NPD6903	Approved
0.6966	Remote Similarity	NPD6098	Approved
0.6932	Remote Similarity	NPD3665	Phase 1
0.6932	Remote Similarity	NPD3666	Approved
0.6932	Remote Similarity	NPD3133	Approved
0.6897	Remote Similarity	NPD4221	Approved
0.6897	Remote Similarity	NPD4223	Phase 3
0.6875	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6928	Phase 2
0.6813	Remote Similarity	NPD5208	Approved
0.68	Remote Similarity	NPD6675	Approved
0.68	Remote Similarity	NPD5739	Approved
0.68	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD6402	Approved
0.6782	Remote Similarity	NPD4692	Approved
0.6782	Remote Similarity	NPD4139	Approved
0.6742	Remote Similarity	NPD4786	Approved
0.6742	Remote Similarity	NPD4197	Approved
0.6739	Remote Similarity	NPD6673	Approved
0.6739	Remote Similarity	NPD6080	Approved
0.6739	Remote Similarity	NPD6904	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6737	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1700	Approved
0.6733	Remote Similarity	NPD5701	Approved
0.6733	Remote Similarity	NPD5697	Approved
0.6705	Remote Similarity	NPD3667	Approved
0.6702	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6634	Remote Similarity	NPD6008	Approved
0.6632	Remote Similarity	NPD6001	Approved
0.663	Remote Similarity	NPD6672	Approved
0.663	Remote Similarity	NPD5737	Approved
0.6628	Remote Similarity	NPD4238	Approved
0.6628	Remote Similarity	NPD4802	Phase 2
0.6602	Remote Similarity	NPD6014	Approved
0.6602	Remote Similarity	NPD6372	Approved
0.6602	Remote Similarity	NPD6013	Approved
0.6602	Remote Similarity	NPD6373	Approved
0.6602	Remote Similarity	NPD6012	Approved
0.6596	Remote Similarity	NPD5281	Approved
0.6596	Remote Similarity	NPD5693	Phase 1
0.6596	Remote Similarity	NPD5284	Approved
0.6593	Remote Similarity	NPD4690	Approved
0.6593	Remote Similarity	NPD5205	Approved
0.6593	Remote Similarity	NPD4688	Approved
0.6593	Remote Similarity	NPD4693	Phase 3
0.6593	Remote Similarity	NPD4689	Approved
0.6593	Remote Similarity	NPD4138	Approved
0.6538	Remote Similarity	NPD7102	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6535	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7638	Approved
0.6489	Remote Similarity	NPD5207	Approved
0.6489	Remote Similarity	NPD5692	Phase 3
0.6476	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6650	Approved
0.6476	Remote Similarity	NPD6847	Approved
0.6476	Remote Similarity	NPD6649	Approved
0.6476	Remote Similarity	NPD8130	Phase 1
0.6476	Remote Similarity	NPD6869	Approved
0.6476	Remote Similarity	NPD6617	Approved
0.6465	Remote Similarity	NPD8418	Phase 2
0.6465	Remote Similarity	NPD7640	Approved
0.6465	Remote Similarity	NPD7639	Approved
0.6458	Remote Similarity	NPD7748	Approved
0.6437	Remote Similarity	NPD3617	Approved
0.6429	Remote Similarity	NPD4755	Approved
0.6421	Remote Similarity	NPD5694	Approved
0.6421	Remote Similarity	NPD6050	Approved
0.6415	Remote Similarity	NPD6882	Approved
0.6415	Remote Similarity	NPD8297	Approved
0.6413	Remote Similarity	NPD3618	Phase 1
0.6413	Remote Similarity	NPD5280	Approved
0.6413	Remote Similarity	NPD5690	Phase 2
0.6413	Remote Similarity	NPD4694	Approved
0.6392	Remote Similarity	NPD4629	Approved
0.6392	Remote Similarity	NPD5210	Approved
0.6383	Remote Similarity	NPD5328	Approved
0.6383	Remote Similarity	NPD6051	Approved
0.6351	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7632	Discontinued
0.63	Remote Similarity	NPD5286	Approved
0.63	Remote Similarity	NPD5285	Approved
0.63	Remote Similarity	NPD4700	Approved
0.63	Remote Similarity	NPD4696	Approved
0.6263	Remote Similarity	NPD5959	Approved
0.6263	Remote Similarity	NPD7902	Approved
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD6079	Approved
0.6239	Remote Similarity	NPD6274	Approved
0.6238	Remote Similarity	NPD5223	Approved
0.6237	Remote Similarity	NPD5279	Phase 3
0.6237	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5654	Approved
0.6207	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4632	Approved
0.6204	Remote Similarity	NPD8133	Approved
0.6196	Remote Similarity	NPD3668	Phase 3
0.6186	Remote Similarity	NPD5133	Approved
0.6182	Remote Similarity	NPD7115	Discovery
0.6182	Remote Similarity	NPD6317	Approved
0.618	Remote Similarity	NPD4195	Approved
0.6176	Remote Similarity	NPD4633	Approved
0.6176	Remote Similarity	NPD5225	Approved
0.6176	Remote Similarity	NPD5224	Approved
0.6176	Remote Similarity	NPD5211	Phase 2
0.6176	Remote Similarity	NPD5226	Approved
0.6154	Remote Similarity	NPD6920	Discontinued
0.6132	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6313	Approved
0.6126	Remote Similarity	NPD6314	Approved
0.6126	Remote Similarity	NPD6335	Approved
0.6118	Remote Similarity	NPD4243	Approved
0.6117	Remote Similarity	NPD5174	Approved
0.6117	Remote Similarity	NPD4754	Approved
0.6117	Remote Similarity	NPD5175	Approved
0.6111	Remote Similarity	NPD4748	Discontinued
0.6111	Remote Similarity	NPD7525	Registered
0.6095	Remote Similarity	NPD6412	Phase 2
0.6075	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7101	Approved
0.6071	Remote Similarity	NPD3726	Approved
0.6071	Remote Similarity	NPD3725	Approved
0.6071	Remote Similarity	NPD7100	Approved
0.6058	Remote Similarity	NPD5141	Approved
0.6044	Remote Similarity	NPD5369	Approved
0.6036	Remote Similarity	NPD6009	Approved
0.602	Remote Similarity	NPD8171	Discontinued
0.6018	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD5221	Approved
0.5979	Remote Similarity	NPD4096	Approved
0.5978	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6435	Approved
0.5977	Remote Similarity	NPD4784	Approved
0.5977	Remote Similarity	NPD4785	Approved
0.5972	Remote Similarity	NPD2266	Phase 2
0.5965	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5983	Phase 2
0.5965	Remote Similarity	NPD6909	Approved
0.5965	Remote Similarity	NPD6908	Approved
0.5962	Remote Similarity	NPD6052	Approved
0.596	Remote Similarity	NPD7900	Approved
0.596	Remote Similarity	NPD7901	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data